Bench-Stable SO2 Surrogate for Sulfonation and Sulfamination

DABSO (Bis(sulfur dioxide)-1,4-diazabicyclo[2.2.2]octane Adduct, TCI code B3960) is a bench-stable solid that serves as a sulfur dioxide surrogate.¹) ²) It can be used with metal catalysts and applied to the syntheses of various sulfone derivatives. DABSO has been used in sulfonation, sulfamination, sulfonyl fluoride synthesis, sulfamidation and sulfoxidation.³) ⁴) ⁵) ⁷) ⁸) As a practical example, a nickel-catalyzed three-component reaction of 4-biphenylboronic acid, DABSO and tert-butyl bromoacetate, using NiBr2(glyme) with tmphen in DMI at 100 °C for 14 hours, was performed. Tert-butyl bromoacetate was added after the mixture was cooled, and the sulfone product was obtained in 76% yield.

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References

1. Y. Chen, M. C. Willis, Chem. Sci. 2017, 3249. doi:https://doi.org/10.1039/C6SC05483H
2. A. Shavnya, A. C. Smith, et al., Angew. Chem. Int. Ed. 2015, 54, 13571. doi:https://doi.org/10.1002/anie.201505918
3. H. Woolven, M. C. Willis, et al., Org. Lett. 2011, 13, 4876. doi:https://doi.org/10.1021/ol201957n
4. A. S. Tsai, V. Mascitti, et al., Org. Lett. 2016, 18, 508. doi:https://doi.org/10.1021/acs.orglett.5b03545
5. M. W. Johnson, F. D. Toste, et al., Angew. Chem. Int. Ed. 2014, 53, 4404. doi:https://doi.org/10.1002/anie.201400037
6. T. Markovic, M. C. Willis, et al., Chem. Sci. 2017, 8, 4437. doi:https://doi.org/10.1039/C7SC00675F
7. D. C. Lenstra, M. C. Willis, et al., Org. Lett. 2016, 18, 2086. doi:https://doi.org/10.1021/acs.orglett.6b00712
8. A. L. Tribby, N. D. Ball, et al., J. Org. Chem. 2017, 82, 2294. doi:https://doi.org/10.1021/acs.joc.7b00051

Download TCI brochure Sulfur Dioxide (SO2) Surrogate Reagents Usable for Sulfonation (PDF)

Source

• TCI Practical Example: www.tcichemicals.com/ID/en/product/tci-topics/TCIPracticalExample_20250127
• TCI product page B3960: tcichemicals.com/ID/en/p/B3960
• TCI product page P2480: tcichemicals.com/ID/en/p/P2480
• TCI brochure RR110: Sulfur Dioxide (SO2) Surrogate Reagents Usable for Sulfonation

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